Hawaii · SAILING IN THE BIG ISLAND

15 Sailing in the Big Island Worth Booking

30 tours  ·  from $80 a head

Good sailing in the Big Island fill up weeks ahead and the great ones go first. Below: the 15 to book early, what each includes and how they differ.

Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch - What the power catamaran adds
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Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch

1.Captain Cook Snorkel On A Power Catamaran With Lunch

★★★★★★★★★★5.0 · 2,232 reviews · 4 hours (approx.) · from $85Our pick

Join Hang Loose Boat Tours for a four-hour catamaran trip from Kona to historic Kealakekua Bay. Captain Aiden, Captain Bryce, Jordan, and the crew guide you to clear water filled with reef fish and coral, with dolphins or winter humpback whales possible along the way. Gear, lunch, drinks, and a boat slide are included.

“Jordan went far beyond in helping my wife and I He is the best Perk and Judy would say he is the best back hand you have”

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Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona - Red Hill snorkeling: know what you are booking
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Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona

2.Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona

★★★★★★★★★★5.0 · 797 reviews · 4 hours 30 minutes (approx.) · from $183

Board Body Glove’s large catamaran from Kailua-Kona for a 4.5-hour outing along the Gold Coast. You’ll get breakfast, lunch, snorkel gear, reef-safe sunscreen, about two hours in the water, and a good chance to spot dolphins or seasonal whales. Captain Erica, Adam, Brianna, and Taylor have all been praised for attentive service, though the Red Hill snorkel site is not Kealakekua Bay.

“There were many snorkeling companies, but I never regret choosing this.The staff were super kind and the breakfast and lunch they provided were so delicious with fresh ingredients. On the way to the snorkeling spot, we could see a group of dolphins. Besides snorkeling, they provided various swimming equipment for children to enjoy. It was a very satisfying experience and I want to do it again!!”

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Afternoon Sail & Snorkel to the Captain Cook Monument - The Captain Cook Monument from the water
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Afternoon Sail & Snorkel to the Captain Cook Monument

3.Afternoon Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 722 reviews · 3 hours (approx.) · from $136

Join Sea Paradise at 1:45 pm for a three-hour afternoon sail from Keauhou Bay to Kealakekua Bay. You will receive snorkel gear, flotation aids, reef-safe sunscreen, snacks, and drinks. A crew-led snorkel outing, cultural stories, and possible dolphin sightings round out the trip. Alcohol is available to buy afterward.

“Great snorkel and sail experience! Such a blast and all of the crew was great! I highly recommend this tour.”

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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure - Sailing south along the Kona coast
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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

4.Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

★★★★★★★★★★5.0 · 695 reviews · 4 hours (approx.) · from $189

Sail Kona’s coast on Kona Style’s 50-foot catamaran to Kealakekua Bay, where you’ll receive snorkel gear, safety instruction, and about an hour in the marine sanctuary near the Captain Cook Monument. Breakfast, Kona coffee, lunch, drinks, flotation noodles, and Hawaiian history are included. The morning starts at 8:30 a.m. in Kailua-Kona.

“About an hour along the coast to the snorkel site, about an hour snorkeling, and then back (with a few stops along the way). Knowledgable and friendly crew. Stunningly clear and beautiful water. Colorful array of fish and sea life…. Great excursion!”

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Deluxe Sail & Snorkel to the Captain Cook Monument - Breakfast, coast views, and a useful start to the day
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Deluxe Sail & Snorkel to the Captain Cook Monument

5.Deluxe Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 535 reviews · 4 hours 30 minutes (approx.) · from $177

Set out from Keauhou Bay aboard Sea Paradise’s catamaran for a 4.5-hour morning cruise along the Kona coast. You’ll snorkel at Red Hill and Captain Cook Monument in Kealakekua Bay, with gear, reef-safe sunscreen, breakfast, lunch, snacks, and guidance included. Captain T-Roy and crew members such as Beau, Denali, Bailee, and Noe have been praised for their friendly support.

“Amazing grew, fun afternoon. Wish we hadn’t gone a day after a storm - try to go when it’s good visibility, but we still saw nice fish and had fun riding on the boat. Thanks!”

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Deluxe Sail & Snorkel to the Captain Cook Monument - Breakfast, coast views, and a useful start to the day
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Deluxe Sail & Snorkel to the Captain Cook Monument

6.Deluxe Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 472 reviews · 4 hours 30 minutes (approx.) · from $179

Sail from Keauhou Bay aboard Sea Paradise’s catamaran for two snorkel stops near Captain Cook Monument and Red Hill. You get breakfast, lunch, snacks, drinks, gear, reef-safe sunscreen, and fish ID cards. The crew, including captains such as Troy, Mike, and Micah, keeps the outing friendly and safety-focused.

“Excellent crew, great little trip! The ride was amazing, they told us a little backstory about the monument we saw, they were very friendly and approachable. The atmosphere was chill, easygoing, we had enough time to explore the reef, we saw and swum with the dolphins! Definitely worth it!”

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Waikoloa Signature Catamaran Sunset Sail - A smooth ride along the Kohala-Kona coast
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Waikoloa Signature Catamaran Sunset Sail

7.Waikoloa Signature Catamaran Sunset Sail

★★★★★★★★★★4.5 · 396 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $159

Sail from Anaehoomalu Bay aboard a 53-foot catamaran for sunset views along the Kohala-Kona coast. The 90-minute cruise includes a premium bar, snacks, shaded seating, restrooms, and live commentary. You board barefoot by tender boat, with room for up to 49 people.

“We had a great cruise. The crew was terrific. We enjoyed the catamaran. The drinks were varied and the dinner was a surprise.”

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Afternoon Sail & Snorkel to the Captain Cook Monument - The Captain Cook Monument from the water
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Afternoon Sail & Snorkel to the Captain Cook Monument

8.Afternoon Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 246 reviews · 3 hours (approx.) · from $136

Set out from Keauhou Bay at 2 p.m. aboard Sea Paradise’s trimaran for a three-hour sail and snorkel at Kealakekua Bay. You’ll receive gear, reef-safe sunscreen, drinks, and snacks, then swim near the Captain Cook Monument in a protected marine sanctuary. The crew offers help for beginners, shares Hawaiian history, and may point out spinner dolphins along the coast.

“The crew staff was amazing! Snorkeling was fun! The staff took the time to explain and of a quick training on snorkeling.”

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Kona Signature Catamaran Sunset Sail - Drinks, snacks, and the surprise dinner
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Kona Signature Catamaran Sunset Sail

9.Kona Signature Catamaran Sunset Sail

★★★★★★★★★★5.0 · 218 reviews · 1 hour 30 minutes (approx.) · from $109

Sail from Honokohau Harbor along the Kona Coast for about 90 minutes aboard a spacious catamaran. Captain Michael and crew members such as Caesar, John, Xander, Nicole, and Kevin have helped create a friendly, relaxed outing. Expect shaded and open seating, a restroom, snacks, drinks, and possible dolphin or whale sightings.

“The boat was awesome. The crew was a lot of fun. The food was really great and the views were unmatched.”

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Kailua-Kona: Captain Cook Reef Catamaran Day Trip with Lunch - Cruising toward Kealakekua Bay
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Kailua-Kona: Captain Cook Reef Catamaran Day Trip with Lunch

10.Kona: Captain Cook Reef Catamaran Day Trip with Lunch

★★★★★★★★★★4.8 · 189 reviews · 4 hours - 270 minutes · from $80Best value

Cruise from Honokohau Harbor to Captain Cook Monument with guides such as Bryce, AJ, Aidan, and Kelly. You get snacks, drinks, sandwiches, and fresh fruit, plus snorkeling gear if you choose that option. Expect a lively four-hour ride, local history, reef fish, and possible dolphin or whale sightings.

“The whole team was amazing, we will be back for sure…”

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Waikoloa Catamaran Snorkel Sail Including Lunch - Snorkeling along the Waikoloa and Kohala Coast
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Waikoloa Catamaran Snorkel Sail Including Lunch

11.Waikoloa Catamaran Snorkel Sail Including Lunch

★★★★★★★★★★4.5 · 105 reviews · 3 hours (approx.) · from $189

Set sail from Anaeho'omalu Bay aboard the Spirit of Aloha for a 3-hour Waikoloa catamaran trip. You’ll receive snorkel gear, flotation equipment, safety help, lunch, snacks, and a full bar. The crew may spot turtles, dolphins, whales, and rays, though wildlife and water conditions vary.

“One of the best snorkeling trips we’ve done in Hawaii! The reef was awesome with many species of beautiful fish. The water was a little rough, but the crew did an excellent job of keeping an eye on everyone. The boat was clean and the entire crew was fun and hospitable. Lunch was great after snorkeling, and they even accommodated my request for a vegan meal, which was much appreciated. We will book with them again!”

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Kona Catamaran Snorkel Sail with Lunch - Snorkeling from the catamaran
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Kona Catamaran Snorkel Sail with Lunch

12.Kona Catamaran Snorkel Sail with Lunch

★★★★★★★★★★5.0 · 101 reviews · 3 hours (approx.) · from $169

Spend about three hours aboard Hawaii Nautical’s Spirit of Aloha from Honokohau Harbor. You’ll sail the Kona Coast, snorkel from the catamaran with provided gear, and enjoy sandwiches, tropical cocktails, beer, wine, soda, and juice. Captains and mates such as Michael, Keith, Nicole, and Isaiah are known for close help in the water.

“Incredible experience. Michael and Kyle were awesome and made us feel right at home on the “No Wiki.” They both gave us a lovely tour of the coastline of Kona and also gave great snorkeling tips and instructions. 12/10 highly recommend this tour. We saw plenty of tangs, a few parrot fish and an octopus! The best part however, were the spinner dolphins Michael was able to locate several times. Very cool experience.”

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Waikoloa: Catamaran Sunset Sail with Cocktails - A sunset sail built around the view
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Waikoloa: Catamaran Sunset Sail with Cocktails

13.Catamaran Sunset Sail with Cocktails

★★★★★★★★★★4.8 · 68 reviews · 1h 30m · from $159

Sail from Anaehoomalu Bay aboard Hawaii Nautical’s Spirit of Aloha catamaran for a 90-minute sunset cruise. Captain Michael and the local crew serve tropical cocktails, beer, wine, soft drinks, water, and island-style snacks while you watch the Kohala Coast, Mauna Kea, Hualalai, and the Pacific sunset. Boarding involves a short barefoot step through seawater from a tender boat.

“Everything about the sunset sail was awesome. Beautiful sailing and sunset; as well as expert/kind/wonderful captain and crew. I couldn’t have enjoyed it more.”

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Sunset Cocktail Cruise on our Sailing Catamaran - What happens from check-in to sunset
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Sunset Cocktail Cruise on our Sailing Catamaran

14.Sunset Cocktail Cruise on our Sailing Catamaran

★★★★★★★★★★5.0 · 62 reviews · 2 hours (approx.) · from $165

Spend about two hours cruising the Kohala Coast aboard Ocean Sports’ catamaran. You’ll get ocean sunset views, unlimited soft drinks, beer, wine, cocktails, and hot and cold pupus. The boat may sail or run under power, depending on the vessel and date. Departure can be from ʻAnaehoʻomalu Bay or Kawaihae Harbor.

“We decided to finish out our vacation with this relaxing cruise at sunset. It was a perfect way to close out our trip. The staff was great and very attentive.”

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Kona Deluxe Catamaran Whale Watch - Watching humpbacks in Hawaiian waters
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Kona Deluxe Catamaran Whale Watch

15.Kona Deluxe Catamaran Whale Watch

★★★★★★★★★★4.5 · 55 reviews · 1 hour 30 minutes (approx.) · from $109

Cruise from Honokohau Marina aboard the Spirit of Aloha, a comfortable catamaran carrying up to 49 people. The crew points out humpback whales, dolphins, and other marine life while serving tropical cocktails, beer, wine, soda, and juice. Stan, John, James, Ali, Michael, and Captain Kirk have all been praised for warm service, though crew assignments can change.

“The best part was seeing whales. The crew was very good. The weather was great. Would recommend to anyone.”

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New in Sailing in the Big Island

★ 5.0Afternoon Tradewind Sail from WaikoloaFrom $11710 reviews
★ 5.0Hawaiian Sail and Snorkel in Kailua-Kona, HawaiiFrom $12510 reviews
★ 5.0Luxury Catamaran Trip along the Kona CoastFrom $4495 reviews
★ 4.4Kona Deluxe Catamaran Whale Watching CruiseFrom $10918 reviews
★ 4.9Kona Turtle Snorkel Sail with Lunch and DrinksFrom $16919 reviews
★ 5.0Kona: Kealakekua Bay Snorkel and Sail with LunchFrom $1885 reviews
★ 5.0Kona: Manta Ray Snorkeling and Sunset Sailing CruiseFrom $1543 reviews
★ 4.7Kona Tradewind Catamaran Sail with CocktailsFrom $895 reviews
★ 5.0Catamaran Sunset Sail with Cocktails and SnacksFrom $1098 reviews

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